CS225599B1 - 2,3,10,ll-Tetramethoxy-6-(4-tolyl)berbin a jeho hydrochlorid - Google Patents

2,3,10,ll-Tetramethoxy-6-(4-tolyl)berbin a jeho hydrochlorid Download PDF

Info

Publication number: CS225599B1
Authority: CS; Czechoslovakia
Prior art keywords: hydrochloride; tolyl; mixture; tetramethoxy; berbine
Prior art date: 1982-11-03

Application number

CS782682A

Other languages

Czech (cs)

English (en)

Inventor

Vladimir Ing Csc Valenta

Miroslav Dr Ing Drsc Protiva

Original Assignee

Valenta Vladimir

Protiva Miroslav

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1982-11-03

Filing date

1982-11-03

Publication date

1984-02-13

1982-11-03 Application filed by Valenta Vladimir, Protiva Miroslav filed Critical Valenta Vladimir

1982-11-03 Priority to CS782682A priority Critical patent/CS225599B1/sk

1984-02-13 Publication of CS225599B1 publication Critical patent/CS225599B1/sk

Links

VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 title claims description 16
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 title claims description 4
BRLDZKPJJNASGG-KRWDZBQOSA-N alpha-berbine Chemical compound C1=CC=C2CN3CCC4=CC=CC=C4[C@@H]3CC2=C1 BRLDZKPJJNASGG-KRWDZBQOSA-N 0.000 title description 2
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
239000000203 mixture Substances 0.000 description 13
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 10
150000001875 compounds Chemical class 0.000 description 8
238000002844 melting Methods 0.000 description 8
230000008018 melting Effects 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
SWCZIXGXWUQGHG-UHFFFAOYSA-N 1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-3-(4-methylphenyl)-1,2,3,4-tetrahydroisoquinoline;hydrochloride Chemical compound Cl.C1=C(OC)C(OC)=CC=C1CC1C2=CC(OC)=C(OC)C=C2CC(C=2C=CC(C)=CC=2)N1 SWCZIXGXWUQGHG-UHFFFAOYSA-N 0.000 description 6
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
239000000155 melt Substances 0.000 description 6
238000000354 decomposition reaction Methods 0.000 description 5
239000000126 substance Substances 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
239000002585 base Substances 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
238000012512 characterization method Methods 0.000 description 4
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
229910000041 hydrogen chloride Inorganic materials 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
QBJIMTPENIGDOG-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)acetyl chloride Chemical compound COC1=CC=C(CC(Cl)=O)C=C1OC QBJIMTPENIGDOG-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
230000000845 anti-microbial effect Effects 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
239000000463 material Substances 0.000 description 3
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000012043 crude product Substances 0.000 description 2
238000000605 extraction Methods 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000000047 product Substances 0.000 description 2
239000000523 sample Substances 0.000 description 2
239000003204 tranquilizing agent Substances 0.000 description 2
230000002936 tranquilizing effect Effects 0.000 description 2
UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical class C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 1
KFDBOENRVXPIPH-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-1-(4-methylphenyl)ethanamine Chemical compound C1=C(OC)C(OC)=CC=C1CC(N)C1=CC=C(C)C=C1 KFDBOENRVXPIPH-UHFFFAOYSA-N 0.000 description 1
PGZNIWQFERVMKP-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-1-(4-methylphenyl)ethanone Chemical compound C1=C(OC)C(OC)=CC=C1CC(=O)C1=CC=C(C)C=C1 PGZNIWQFERVMKP-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
LTHAWQZXDKSDMD-UHFFFAOYSA-N 6,8,13,13a-tetrahydro-5h-isoquinolino[2,1-b]isoquinoline;hydrochloride Chemical compound Cl.C1=CC=C2CN3CCC4=CC=CC=C4C3CC2=C1 LTHAWQZXDKSDMD-UHFFFAOYSA-N 0.000 description 1
241000228245 Aspergillus niger Species 0.000 description 1
241000222122 Candida albicans Species 0.000 description 1
241000233866 Fungi Species 0.000 description 1
231100000111 LD50 Toxicity 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
-1 N- [2- (3,4-dimethoxyphenyl) -1- (4-tolyl) ethyl] -3,4-dimethoxyphenylacetamide Chemical compound 0.000 description 1
238000006929 Pictet-Spengler synthesis reaction Methods 0.000 description 1
241000700159 Rattus Species 0.000 description 1
241000235070 Saccharomyces Species 0.000 description 1
240000004808 Saccharomyces cerevisiae Species 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
IUJDSEJGGMCXSG-UHFFFAOYSA-N Thiopental Chemical compound CCCC(C)C1(CC)C(=O)NC(=S)NC1=O IUJDSEJGGMCXSG-UHFFFAOYSA-N 0.000 description 1
239000000538 analytical sample Substances 0.000 description 1
238000004166 bioassay Methods 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229940095731 candida albicans Drugs 0.000 description 1
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
238000001035 drying Methods 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
230000000147 hypnotic effect Effects 0.000 description 1
230000002631 hypothermal effect Effects 0.000 description 1
239000005457 ice water Substances 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
238000000034 method Methods 0.000 description 1
150000004682 monohydrates Chemical class 0.000 description 1
GFBZBTGJEJNXJN-UHFFFAOYSA-N n-[2-(3,4-dimethoxyphenyl)-1-(4-methylphenyl)ethyl]formamide Chemical compound C1=C(OC)C(OC)=CC=C1CC(NC=O)C1=CC=C(C)C=C1 GFBZBTGJEJNXJN-UHFFFAOYSA-N 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
150000002923 oximes Chemical class 0.000 description 1
230000001717 pathogenic effect Effects 0.000 description 1
230000003285 pharmacodynamic effect Effects 0.000 description 1
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000002994 raw material Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000012265 solid product Substances 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
229960003279 thiopental Drugs 0.000 description 1
229940125725 tranquilizer Drugs 0.000 description 1
238000005406 washing Methods 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CS782682A 1982-11-03 1982-11-03 2,3,10,ll-Tetramethoxy-6-(4-tolyl)berbin a jeho hydrochlorid CS225599B1 (sk)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CS782682A CS225599B1 (sk)	1982-11-03	1982-11-03	2,3,10,ll-Tetramethoxy-6-(4-tolyl)berbin a jeho hydrochlorid

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CS782682A CS225599B1 (sk)	1982-11-03	1982-11-03	2,3,10,ll-Tetramethoxy-6-(4-tolyl)berbin a jeho hydrochlorid

Publications (1)

Publication Number	Publication Date
CS225599B1 true CS225599B1 (sk)	1984-02-13

Family

ID=5428102

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS782682A CS225599B1 (sk)	1982-11-03	1982-11-03	2,3,10,ll-Tetramethoxy-6-(4-tolyl)berbin a jeho hydrochlorid

Country Status (1)

Country	Link
CS (1)	CS225599B1 (sk)

1982
- 1982-11-03 CS CS782682A patent/CS225599B1/sk unknown

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